Inside Union Correctional Institution in Raiford, a man with drooping, yellowed skin and graying temples sits for 23 hours a day, every day. He eats a hot meal at 5 a.m., 10:30 and 4 p.m. Once every other day, he showers. The rest of the time, he is alone in a sweltering 6- by 9-foot cell, thinking whatever thoughts run through the mind of a man who once claimed transsexual communist agents were trying to poison his food.

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His name is Gary Alvord. For almost 40 years, he has waited out a death sentence he received for the 1973 murders of three women in Tampa. Today, the 66-year-old holds the distinction of having been a member of death row longer than any other inmate in America.

He has survived eight presidents, nine governors and two death warrants. Since his arrival on death row, Alvord has seen 74 other inmates continue on to the execution chamber. Of those who have been executed in the last decade, the average length of stay on death row has been about 20 years — half as long as Alvord.

So why is Gary Alvord still alive?

The simple answer is that he is crazy. For most of his life, Alvord has been plagued by delusions and disordered thoughts that doctors have most often attributed to schizophrenia and antisocial personality disorder. His condition, lawyers have argued, makes him incapable of understanding capital punishment.

The law forbids the execution of anyone with such a mental condition. At the same time, the state lacks the political willpower to do anything other than allow Alvord to linger on death row.

His case is not unique. In Florida and nationwide, death row is full of inmates whose mental condition makes it difficult, if not impossible, to execute them. Yet, over and over, such men are condemned to death.

On Tuesday, in a Colorado court, lawyers for James Holmes may enter a plea of not guilty by reason of insanity. Holmes is accused of a shooting rampage last summer at a movie theater, killing 12 and injuring 58. Prosecutors in that case have indicated that they might seek the death penalty.

Like Alvord's, Holmes' case exposes a paradox inherent to the American death penalty system — we demand the ultimate punishment for those who commit terrible crimes, but we permit a measure of mercy for those who don't understand their actions or their penalty.

Gary Alvord ended up on death row because he is crazy. And, in all likelihood, he will never be executed for the very same reason.

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The son of a reportedly abusive father and a mother who suffered recurring mental breakdowns, Alvord spent much of a his childhood in institutions in his native Michigan. In 1960, at age 13, he was sent to live in a state mental hospital.

As he grew, doctors noted clear signs that the young man was disturbed. He threatened to kill doctors and other patients. He tried to escape from the hospital numerous times. After one escape, he was alleged to have been involved in a shooting. Those who knew him say he was a prolific thief.

In 1967, while on release, he kidnapped and raped a 10-year-old girl.

As he awaited trial, Alvord was hospitalized after he swallowed five spoons, a razor blade, nuts and bolts, shower attachments and empty rolled-up toothpaste tubes. He said that "voices from the spirit world" told him that the objects he swallowed would cure "cuts, cancer and other illnesses."

In medical records and court testimony, psychiatrists said Alvord "lacks remorse," and described him as "dangerous" and "not in touch with reality."

He stood trial for the rape in 1970. A psychiatrist testified that Alvord didn't know right from wrong. A jury found him not guilty by reason of insanity and he was sent back to a state hospital.

In January 1973, he escaped again.

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Alvord surfaced in Tampa. He befriended several people, found a girlfriend, and moved into her Davis Islands apartment.

He became a regular at the Guys and Dolls Billiard Hall on Kennedy Boulevard. There, he met Ann Herrmann, 36, the owner of the business. One day, a man Alvord knew bickered with Herrmann about the price of a pool game. A witness later heard Alvord confront her.

"Usually when somebody rips off my friends, I kill them," he said.

On June 18, 1973, authorities found the bodies of Herrmann, her daughter Lynn Herrmann, 18, and Herrmann's mother, Georgia Tully, 53, inside a home off N Florida Avenue. They had been strangled to death. Lynn Herrmann was also raped.

Alvord, detectives learned, confessed the murders to his girlfriend and showed her cash and other items he had stolen from the home. The couple fled north, but Alvord's girlfriend returned to Florida, where she told detectives what she knew. Police later arrested Alvord in Michigan.

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Physical evidence and witness testimony left little doubt about Alvord's guilt. The case's bigger question, one that attorneys and a judge grappled with in the months leading up to his trial, had to do with his state of mind both at the time of the murders and in court.

Alvord refused to cooperate with his public defender, Tom Meyers, and told a judge he didn't want to use an insanity defense. Two psychiatrists tried to examine him, but he wouldn't cooperate with them either.

At the court's request, Dr. Ames Robey, a Michigan psychiatrist who had previously treated Alvord, visited him in jail. Robey testified that Alvord understood his legal situation and that his reluctance to cooperate was not due to mental illness.

"The evidence for schizophrenia in Gary is not the kind that a layman would pick up," Robey testified. "(He is) not clearly, overtly mentally ill, but certainly leaning quite far over that way."

Subsequent input from two other psychiatrists led Judge Robert W. Rawlins to permit Alvord's trial without an insanity defense. Alvord was convicted. A majority of the jurors recommended death and Rawlins agreed.

He wrote: "You are to be confined within the walls of the permanent death chamber pending execution by the passage through your body of a current of electricity of sufficient intensity to cause death as provided under the laws of the state of Florida.

"May God have mercy on your soul."

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Two years earlier, the U.S. Supreme Court had ruled that the death penalty was unconstitutionally cruel and unusual punishment. Florida amended its death penalty statute, enabling judges to continue to impose death sentences.

When states were given the go-ahead to resume executions in 1976, Alvord was at the top of the list. But he was passed over in favor of John Spenkelink, who in 1979 became the first man since the constitutional repeal to die in Florida's electric chair.

In 1981, Gov. Bob Graham signed Gary Alvord's first death warrant. A federal court issued a stay.

In 1984, Graham signed a second death warrant, setting Alvord's execution for Nov. 29.

On Nov. 20, Alvord's appellate attorney, William Sheppard of Jacksonville, filed an appeal with the Florida Supreme Court. He detailed his client's mental illness, which, he said, had worsened over the years from lack of treatment.

Alvord was "unresponsive to outside stimulus," Sheppard said. In rambling letters to attorneys and state officials, Alvord referred to himself as "Lactoo-decendent of the I."

"As Lactoo, he believes he has been tortured since early childhood by communist agents who are attempting to destroy the Polish race," Sheppard wrote.

"In the last few weeks, Mr. Alvord has begun to believe that his counsel is not an attorney but is instead, a double agent. Assistant Attorney General Carolyn Snurkowski is the object of many of Mr. Alvord's delusions (he believes she is a transsexual agent from Poland), as is Gov. Graham."

Graham ordered Alvord examined by a panel of three psychiatrists, in accordance with state law. The doctors said Alvord was insane and he was sent to a state hospital at Chattahoochee.

But doctors there refused to treat Alvord, citing the ethical dilemma of trying to make someone well just so he could be killed.

Alvord lingered in Chattahoochee for three years. His illness, though not cured, had stabilized with medication. He was quietly moved back to death row, where he again refused to cooperate with a panel of psychiatrists assigned to assess his competence.

Through the 1990s, Sheppard filed more appeals, arguing that an insanity defense should have been permitted at trial. None succeeded. His last appeal, a petition to the U.S. Supreme Court, was denied in 1998. Theoretically, Gov. Rick Scott could sign a third death warrant for Alvord at any time.

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So why is Gary Alvord still alive?

The trouble is any attempt to execute him would almost certainly fail. A death warrant would bring about yet another psychological assessment, with which Alvord likely would not cooperate. That assessment could result in his return to Chattahoochee, where doctors would again face the ethical dilemma of treating a condemned man. The process would also trigger a new round of appeals, eating up millions of tax dollars in court-related expenses.

Florida's Office of Executive Clemency, which includes the governor and Cabinet officials, could modify Alvord's sentence to life in prison. But that is unlikely, especially given that no Florida governor since Bob Graham in 1983 has granted clemency to a death row inmate.

"The question is what good will come out of executing the guy?" said Michael Radelet, a University of Colorado professor and a leading expert on the death penalty. "For one, you can't deter the mentally ill. And two, Gary Alvord is completely miserable. Anybody who sees the condition that he's in should applaud in the name of retribution."

Roger Maas, former executive director of the Florida Commission on Capital Cases, said that cases like Alvord's showcase serious problems with the way it is administered in Florida.

"With these kinds of cases, it's kind of a stalemate," Maas, a death penalty supporter, said. "Where's the justice in that?"

Such stalemates are not uncommon. And they're growing.

Last year alone, Florida added 21 new people to its roster of more than 400 death row inmates. It executed three.

At that rate, the majority of death row inmates will die of natural causes.

In October, a federal appeals court blocked the execution of another Florida inmate, John Ferguson, who has been on death row since 1978. Convicted in the slayings of eight people in South Florida, Ferguson has also been the subject of questions about his sanity. He, too, suffers from schizophrenia and is said to believe that he is the "Prince of God."

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The problem, Maas said, is a legislative one. Death penalty statutes allow for too many "aggravating factors" — circumstances that qualify capital punishment as an appropriate sentence. Death sentences are issued arbitrarily, for murder cases that range widely in their severity.

Legislators could remedy that, but no one wants to touch the issue.

In newer cases, like that of James Holmes, prosecutors are more aware of the legal implications of a death sentence, but it doesn't stop them from seeking it.

"If they do go for death," Radelet said of the Holmes case, "it's going to be a huge battle."

It was a battle in Alvord's case. And there are few voices that decry the outcome. But they are out there.

One is Brenda Brock. She met Gary Alvord in 1966, when she was, as she said, "a young and stupid girl." She knew he had mental problems. Still, she was charmed. They married and had a son.

"I don't know why his mind was so warped," she said. "That's a mysterious part of his life I don't know about. It's heartbreaking on so many levels."

They were divorced by the time he came to death row. Brock remarried, but wrote letters to her ex-husband. In the early 2000s, her notes started coming back unopened. She assumed he had died and was stunned recently to learn that he is still on death row.

"The life he has had might be worse than death," Brock said. "Yet I know Gary is a human being. … To keep a person in a box for 40 years, that's cruel."

Dan Sullivan can be reached at (727) 893-8321 or dsullivan@tampabay.com.